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Power of Pitbull: 'Timber' Rapper Reveals Plan to Become Next Billion-Dollar Brand

Don't underestimate the hitmaker (and new face of Playboy), who talks to THR about life as Cuba's underground hero, why he hasn't talked to Kesha since rehab and how he came to own the pop culture moment.

No offense intended -- truly -- but you can smell Pitbull from a mile away.

It's four days before New Year's Day 2014, and the Cuban-American rapper is performing a concert at Brooklyn's Barclays Center. As showtime nears, hundreds emerge from the subway into a fragrant cloud. There, at the chaotic, multicultural crossroads of Atlantic Avenue and Flatbush, a small army of perfume pushers hand out samples of Pitbull Man and Pitbull Woman, which retail for $30 for a 1 oz. bottle. The scent business is but one of the 33-year-old artist's name-branded products. Also in his portfolio are sponsorships by Dr Pepper, Kodak, Bud Light, Voli Vodka and, most recently, Playboy, which in March tapped Pitbull as the new global face of the half-century-old brand.

Such are the deals that come your way when you score nine top 10 singles, including 2011's "Give Me Everything" and 2013's "Timber," which both reached No. 1 on the Billboard Hot 100 and have sold 8.5 million downloads in the U.S., according to Nielsen SoundScan. With seven albums under his belt, the past four released by Sony Music-owned RCA, Pitbull has merged pop instincts, business acumen and global ambition as profitably as anyone in the entertainment industry right now. And on a frigid New York night in December, he has no problem at all filling 10,000 seats (83 percent capacity).

“It’s a constant fight. Every day, you get up and fight. I mean that in a good way — it’s a way of hustling and being motivated,” says Pitbull of his moniker. Click the photo for more exclusive portraits of Pitbull.

Pitbull does not disappoint his fans. The show is a fist-pumping medley of mostly song snippets -- a verse and chorus of JenniferLopez's 2011 smash "On the Floor," just the hook of Usher's "DJ Got Us Fallin' in Love" from 2010, a few lines of the early-in-Pit's-career "Hotel Room Service" -- along with his own hits, such as "Timber" and "Give Me Everything," featuring Kesha and Ne-Yo, respectively, in video accompaniments. The crowd is an astonishing cross section: Kids and their parents groove alongside sexed-up 20-something couples and so-called cougars on a wild night out with girlfriends.

This is all part of Pit's master plan to follow a path forged by his Cuban predecessors: the musical and cultural icon CeliaCruz, whom he describes as carrying "all of our stories on her back"; the game-changing Latino TV star-turned-mogul DesiArnaz; and '80s and '90s top 40 sensation GloriaEstefan, whom Pitbull praises for "figuring out the business part of it." And he's well on his way, breaking out of the Latin market to rank as one of the world's best-known entertainers. In a carefully choreographed tango that engages both worlds, Pitbull has ordained himself the great persuader, as comfortable in a corporate boardroom as he is on a brightly lit stage.

At a Four Seasons suite in midtown Manhattan the next day, Pitbull explains how a typical corporate sit-down goes: "I'll be sitting in marketing meetings where they're going, 'Well, this is our multicultural budget,' and 'We'll make this a multicultural campaign,' and I say, 'Great!' knowing that they see me in the context of the Latin boom. 'Oh, he's the next Latin this or Latin that. …' But in my mind, I know this is the general market. I touch everybody at the end of the day."

That's no empty brag. In a year, Pitbull can perform in 25 countries and as many as 150 shows (as he did in 2012), touring being one of many revenue streams he pulls in (Forbes estimates Pitbull's net worth at $11 million, but ABC's Nightline puts it at $20 million; sources hint that it's somewhere in the middle). Further proving his international might, Pitbull's "We Are One" has been named the official song of the 2014 World Cup in June in Sao Paulo, Brazil. After the South American jaunt, he'll release an album with CarlosSantana -- a cross-generational play, if ever there was one -- and kick off another U.S. arena trek in the fall with Enrique Iglesias. He'll spend 2015 touring the world again, likely playing stadiums.

One could cite previous Latin popularity crests -- Shakira in her "Hips Don't Lie" days, MarcAnthony or RickyMartin in the 1990s or Pit's repeat song partner Lopez, a perennial on the radio -- as precedents for Pitbull's success. But he aims to be more than the next one in line. The blue-eyed, diminutive millionaire, who flies private everywhere (it's a rental: "There's a rule that says if it flies, floats or f---s, rent it," cracks Pit) in order to fit in as many commitments as humanly possible, has managed to bridge a cultural divide that few in the industry imagined he could when he started out a decade ago.

"In the beginning, I put Pitbull in the 'party music' category and would have earmarked him for a couple of 'turntable' hits," says radio personality Chris Booker of Los Angeles FM station AMP Radio. "Then it felt like he was really working it hard. He was on any platform that would take him, good or bad -- and it paid off. Plus, I've interviewed him, and he is genuinely lovely -- so nice that he's impossible to root against." Adds Elvis Duran, longtime jock at New York pop station Z100: "Pitbull is, in my opinion, one of the most dynamic performers of the last two or three years. When he's onstage, he just chops the trees down. ... And he smells good. We always make it a policy to sniff him."

The Pitbull epic began when his mother, AlyshaAcosta, arrived in Florida from Cuba during the early 1960s as part of Operation Pedro Pan (or Peter Pan), Miami's Catholic Welfare Bureau's two-year effort to get youth out of communist Cuba. His father also came over seeking asylum, settling in Miami's Little Havana neighborhood. Their son Armando was born in 1981, a year in which drug-ravaged Miami recorded 621 homicides and was eulogized in a Time cover story, "Paradise Lost." This was the cocaine cowboy era captured in movies like Scarface.

Pit's father and namesake, known in the neighborhood as a charismatic street hustler, often would take his son to the local bars, where the boy would first perform for an audience, reciting Cuban poetry from a bar stool as his father looked on proudly. Pit's parents divorced in 1985.

Bring up the Brian De Palma classic -- not universally beloved in Miami for the cultural stereotypes it spawned -- and Pitbull takes no umbrage. "We all have Scarfaces in our family," he says matter-of-factly. "[The movie] is the truth. It wasn't exaggerated. Scorsese, OliverStone, De Palma -- those guys were right on the money." Pitbull says he's seen it too many times to count and that a serious message sunk in: that he didn't want to end up like the protagonist Tony Montana. Rather, says Pit: "I wanted to be Sosa -- educated, good-looking, a good dresser, and he's the one who was running it. And notice, he never got his hands dirty. He sipped his tea. He was nice, not aggressive. And at the end of it all, he was the one that stayed. So I realized around 18 that Tony's the wrong guy to be looking up to."

What Pitbull learned from his immediate surroundings, besides how to sell drugs, which he did for a while, was the skill of connecting with people. That's his most powerful gift -- winning loyalty of everyone he encounters, from strangers on the street to dealmakers in a boardroom. He does this, in part, with a relentlessly upbeat attitude. Pitbull explains his six-year rise to the top in the exuberant idiom of a motivational speaker: "2009 is freedom; 2010, invasion; 2011, build empire; 2012, grow wealth; 2013, put the puzzle together; 2014, buckle up; 2015, make history." It's a mantra he shares with manager CharlesChavez, who says his goal is for Pitbull to become a billion-dollar enterprise. "We have a plan -- with the music, TV projects [Pit boasts a development deal with Endemol, producer of Big Brother], films [he's teamed up with RyanSeacrest for a TV miniseries on the Bacardi family], his businesses, the brands that we get involved with," says Chavez. "You never know, but it's the plan."

Pitbull is more confident, even willing to time-stamp the future threshold. "Do I think it's realistic to be a billion-dollar company by [age] 35? Absolutely."

Pitbull already looks upper-crust. Back in 2007, he ditched the corn-rows and baggy T-shirts of his early persona in favor of custom suits, sharp ties and fine leather shoes. He has quite a collection, including preppy wing-tips and moccasins perfect for an afternoon mojito -- or Pitbull's preferred cocktail: a Volito, two parts Voli vodka (he's a partner in the company), three limes, water and ice. He drinks, on average, three to four a day.

As savvy as he comes off in person, the rapper's shtick easily inspires derision, not so much from other artists (who all understand what it takes to sell 3 million albums) but certainly the media. He has taken the name-dropping of brand sponsors to a whole new level of shamelessness and has a propensity for random musings and shout-outs -- hilariously mocked in December on Saturday Night Live by guest host JimmyFallon. A typical jab was in the March 28 issue of Entertainment Weekly: "If Pitbull plays [a concert] and no one is around to care, did it happen?"

This sort of snark was behind the hijacking of a Pitbull-Wal-Mart promotion back in summer 2012. A contest promised to send the rapper to the Wal-Mart store that amassed the most Facebook "likes." As word spread, gangs of nonfans conspired to "exile" Pitbull by voting for a store in Kodiak, Alaska (population 6,457). Pitbull played it by the rules he'd agreed to. Upon arriving at the remote island, where he was greeted by local Alutiiq tribe members and a life-sized stuffed bear, he spoke with humility, telling local news crews that he was "honored" to be there and showing no signs whatsoever of embarrassment.

Pitbull hardly is alone in applying street skills to the building of a music empire (think: Jay Z,Kanye West, Odd Future), but what he has done differently is stay committed to the middle class. You won't find a $900 baseball cap in Pit's future collection, as Jay Z had in his exclusive Barneys line, nor is he selling his fans on a life of excess. Rather, he sings, "We're at the hotel, motel, Holiday Inn." Says Pit: "The only business that I knew growing up was flipping -- if I invested five dollars, I knew I could get back eight. If I got back eight, that meant I could live off three, invest another five, get another eight, stack another three. That's what the music business is to me -- flip after a flip, a flip after a flip."

Applying those same rules to radio wasn't easy as his music was initially considered a problematic hybrid: "Too Latin for hip-hop, too hip-hop for Latin."

Pitbull makes no apologies for his devotion to the genre of his youth. "I fell in love with hip-hop because to me it was therapy," he says. "I could listen to [someone] and go, 'This is happening in his neighborhood, too?' It became my way of getting things off my chest without having to do it physically."

Says longtime Miami radio personality DJ Laz, who was among the first people to play a Pitbull song on the air: "If I told you that every kid could do it, I'd be lying [because] it's very difficult." A 20-year industry veteran, Laz says Pit's first attempts were "so-so," but once Pitbull started name-checking local neighborhoods on such early tracks as "Oye" (from the 2 Fast 2 Furious soundtrack) and "Welcome to Miami," things changed swiftly. Says Laz: "Cities like Mango Hill, Allapattah, places most people would be scared of walking anywhere near, he shouted them out. I remember playing 'Welcome to Miami' on the radio, and people were hitting me up, [saying], 'Laz, he mentioned Mango Hill, he mentioned this, he mentioned that.' … I said, 'Yeah, this kid's the truth!' "

Keeping one foot in the underground and another in Miami's mega dance clubs, Pit started honing a more pop sound. "EDM ran parallel, and now DJs are understanding what it is to make a record," he explains. "Because before, if you go to the clubs, there was, like, a 20-minute f---ing beat, man. Five minutes is just the four-on-the-floor, and then another five minutes is the buildup, and then there's another two minutes of the build to drop, to finally hitting you with what you've been waiting for the whole night. So all I did was say, 'Hmmmm, wait, why don't we take that part, put it here, make that the hook and make that the verse? So now we're getting to everything quicker. Here we go, we have a record."

To take that track to the next level -- meaning, to radio -- Pit relied on his manager Chavez. A burly Houston native who grew up listening to CaseyKasem, writing down the top 40 each week and posting it on his bedroom wall, Chavez says he always has "watched the trends to know what was going on, buying the records, from 45s to albums, and then deejaying everything from skating rinks to clubs to the radio. … I just trained my ear."

It's a trait the 47-year-old shares with his No. 1 client, whom he has represented since 2007. Pit listens carefully for new sounds wherever they might come from. So you might, on one song, hear an Eastern European melody played on an accordion while another is a country hoedown. "As you travel the world, you hear a record somewhere that will take eight months or a year to get to the United States," says Pitbull.

"Timber," which features a harmonica solo paired with Nashville native Kesha's line dance-ready chorus, is an example of honing in on what's breaking elsewhere in the world and importing it back to the U.S. Pitbull divulges that he swiped Swedish DJ Avicii's sound for the tune. "It had the same ring to it," says Pit, referencing the acoustic, country- and blues-tinged melodies on the EDM star's 2013 album, True. "I was like, this is where it's going right now. We need to put this out ASAP. … No one's doing this, we can run right behind it."

DJ Laz wasn't so sure it would connect, giving it a 50-50 shot. Pit welcomed the risk. "I'm not afraid of a flop," he says. "Losing means learning, and a flop means go back in the studio and knock another one out." Dr. Luke, who produced the track with Swedish hitmaker MaxMartin, says he never had any doubts. "It was instantly identifiable," he says. "There was no song like that on the radio."

By year's end, "Timber" ranked in the top 10 in 19 countries, according to Chavez, becoming Pitbull's second-biggest solo hit. (Pit currently is promoting the song "MMM Yeah" by newcomer AustinMahone and "Wild Wild Love" by girl group G.R.L., whom he decided to collaborate with because "they've been grinding for a while.") "Radio is funny," says the manager, noting that at the time, program directors were saying, "There's too much Pitbull on the radio." As Chavez recalls with a laugh: "All of a sudden we give them this 'Timber' song, and it's, 'Oh, there's not enough Pitbull on the radio!' It's all about hits."

In 1999, the principal at Miami's Coral Park High handed an 18-year-old Armando his diploma with a dismissive, "I don't want you coming back to my school next year." In response, Armando rented a photo studio to take his own graduation picture, posing with the diploma, a middle finger and that million-dollar smile. The photo is still at his grandmother's house.

But today, Pitbull is giving children from similar circumstances the chance he never got by opening the Sports Leadership and Management Academy (SLAM!), a public charter school emphasizing sports as a way to connect disenfranchised youth with education, to the tune of $15 million in construction costs. "There is no way that you can tackle any obstacle or any issue around the world if you are not educated," he said in interviews as the school was opening in August. "That's why I fight for it." Pitbull is himself dad to six kids ranging in age from 1 to 11 (he never has married and prefers not to reveal the number of mothers, only to say it's more than one), and parents with one guiding principal: "Pitbull is Pitbull; Papi is Papi," he says. "I teach them that they will never live in my shadow. That they're going to be bigger, better, stronger."

Pitbull is evangelical about hard work. "Why do interns make the best CEOs? Because they got the doughnuts and coffee, they cleaned the bathrooms," he says. "They learned that building in and out." It's a principle that he more than backs up in his own life. In the three months following his Barclays Center bow, he has kept up a relentless pace, including headlining the recent iTunes Music Festival at South by Southwest, after which an inebriated Apple executive professes backstage, "I love you, Pitbull."

While "Timber" spent three consecutive weeks at No. 1, Pit's co-star on the song, Kesha, has been in and out of rehab. Taking a sip of his Volito, Pitbull says they haven't been in touch since she got out of treatment on March 6. "People need their space. The good thing is she came out on a high horse. Sometimes, it's a blessing in disguise."

Although it has been 16 years since he peddled and used drugs -- never cocaine, insists Pitbull, "smoke a joint here and there, have my little drink" -- the experience of abuse still is fresh in his mind. "I grew up around so many alcoholics and drug addicts that I saw early on in my life what I didn't want to do," he says. "I had a mother that went to Alcoholics Anonymous, I sat through the classes. I've seen the 12 steps, the chips, the whole nine."

Talk of Kesha's struggle not only reminds him of those trying teenage days, when his mother threw him out of the house for hanging out with the wrong crowd and dealing, it reaffirms the road he took to get here. "Thank God I didn't have to grow up in the public eye at a time when I was trying to find myself," he says.

Indeed, for Pitbull, success goes hand in hand with being able to handle it -- the timeless notion that says with great power comes great responsibility. He recognizes that not just in himself and his celebrity but beyond the borders of the continental U.S. to the homeland he never has visited: Cuba. There, Pitbull has become an underground hero to millions who have bought his (bootlegged) CDs. He hopes one day to see those fans up close and in person. "I understand them," he says of the connection. "Yes, there is a big disconnect between the generations. We have generations that grew up in it, and those that fought it, came here and built everything again. So when it does open up, my goal is to be ready to be able to handle that."

He envisions a welcome not unlike the pope's 2013 visit to Rio de Janeiro, where people flooded local beaches as far as the eye could see. "To make history in Havana and be able to perform maybe in front of a million, 2 million people, I'm hoping for that within the next five years," he says excitedly. "I can picture it in my mind."